Hotels with Pool & Resorts in Westchester from AU$188

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Westchester Hotels with Pool

This weekend
Next weekend

Our top choices for Westchester hotels with a pool

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,156 reviews)
  • cleanliness
    Splash into the city at this city centre hotel with a sleek indoor pool, stylish loungers, and a vibrant atmosphere to match.
The price is AU$202
includes taxes & fees
6 Apr - 7 Apr
Aloft Chicago Mag Mile

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,041 reviews)
The price is AU$219
includes taxes & fees
5 Apr - 6 Apr
Hilton Chicago/Magnificent Mile Suites

The Hoxton Chicago

The Hoxton Chicago
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Take a dip in the seasonal rooftop pool while sipping craft cocktails at this urban Chicago retreat.
The price is AU$301
includes taxes & fees
5 Apr - 6 Apr
The Hoxton Chicago

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,076 reviews)
  • cleanliness
    Splash into serenity at this Michigan Avenue retreat with a sparkling indoor pool, spa pool haven, and 24-hour fitness centre.
The price is AU$300
includes taxes & fees
9 Apr - 10 Apr
Hyatt Centric Chicago Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,394 reviews)
  • cleanliness
    Seasonal outdoor pool with cabanas and loungers provides sanctuary after exploring Chicago's Magnificent Mile.
The price is AU$202
includes taxes & fees
5 Apr - 6 Apr
DoubleTree by Hilton Chicago - Magnificent Mile

Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Splash into pure relaxation at this city centre hotel's indoor pool with loungers and fitness centre access.
The price is AU$368
includes taxes & fees
10 Apr - 11 Apr
Renaissance Chicago Downtown Hotel

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,769 reviews)
  • cleanliness
    Float away at this stunning luxury hotel with an indoor pool overlooking Lake Michigan and the city's iconic skyline.
The price is AU$287
includes taxes & fees
27 Apr - 28 Apr
The Wade

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,120 reviews)
  • cleanliness
    Indoor pool oasis at upscale Michigan Avenue aparthotel offers year-round swimming enjoyment.
The price is AU$243
includes taxes & fees
5 Apr - 6 Apr
Sentral Michigan Avenue

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (4,412 reviews)
  • cleanliness
    Make a splash at this city centre Chicago hotel with an indoor pool, fitness centre, and stunning city views from each room.
The price is AU$188
includes taxes & fees
12 Apr - 13 Apr
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Homewood Suites by Hilton Chicago-Downtown

Homewood Suites by Hilton Chicago-Downtown
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,156 reviews)
The price is AU$208
includes taxes & fees
19 Apr - 20 Apr
Homewood Suites by Hilton Chicago-Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Choose what matters most at hotels with a pool in Westchester

Top Westchester Hotel Reviews

Frequently asked questions

What are some accommodation options with pools in Westchester?
Congress Plaza Hotel: Hotel, 2-minute walk from Michigan Avenue. Offers an indoor pool and flat-screen televisions. Hilton Chicago/Magnificent Mile Suites: Hotel, 4-minute walk from Michigan Avenue. Provides full, an indoor pool and flat-screen televisions. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 8-minute walk from Lake Michigan. Features a 24-hour fitness centre, an indoor pool and flat-screen televisions. Hotel Riu Plaza Chicago: Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool and complimentary wireless Internet access. Hilton Chicago O'Hare Airport: Hotel, 12-minute walk from Millennium Park. Features 2 restaurants, an indoor pool and a health club.
What is there to see and do in Westchester?
While you're in the area, consider exploring places such as Wrigley Field, United Center and Michigan Avenue. Take a walk along the waterfront at Oak Street Beach and North Avenue Beach. The restaurants and shopping are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Westchester?
You may want to consider a place to stay that has an outdoor pool if you plan to visit Westchester in the hottest months of July, August or June, when the average temp is 22°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is -1°C.